Pressler is a veteran of the Vietnam War. He served two tours of duty as an Army Lieutenant (1967-68), and was awarded a Bronze Star. He was the first returning VietNam veteran to be elected to Congress.

In the 2008 US Presidential Election, Pressler revealed that he had voted via absentee ballot for Democrat Barack Obama, and that he would donate $500 to the Obama/Biden campaign. He claimed to have never before voted for a Democrat, and cited Obama's response to the financial crisis as the primary reason for his decision.[1]